Why He's Betting Everything on a $70M Startup With No Exit Plan | Kevin Coleman - Ravenna.ai

Shamil Malachiyev: Hello everyone, and welcome to today's special birthday episode. With the current speaker, it so happened that we have birthdays on the very same day, and we said, let's shoot a podcast on that day. So with us today we have Kevin from Ravenna. Hi, Kevin.

Kevin Coleman: Hi, Shamil. How are you, man? Happy birthday, first and foremost.

Shamil Malachiyev: Thanks so much, happy birthday to you too!

Kevin Coleman: Man, it was funny when we were talking about this a couple of weeks ago. I was like, my birthday is the 31st. You're like, my birthday is the 31st. I'm like, all right, well, we obviously have to do this on our birthdays.

Shamil Malachiyev: It's probably going to be the only such huge-coincidence episode we'll ever have on the podcast. So it should be a good pod. Can you tell us and the listeners a bit about you and the work that you do with Ravenna?

Kevin Coleman: Yeah, 100%. So my name is Kevin Coleman. I live in Seattle, Washington. I'm one of the co-founders of a company called Ravenna. The company is about a year old. We are building an AI-native internal help desk platform. We help IT, revenue operations and people operations teams, effectively teams who operate internal help or service desks. First and foremost, we give them great software to organize their work that's deeply integrated with Slack, but then we use AI, and also deterministic workflow automation, to help them automate a wide swath of work that they weren't able to previously automate. So, effectively, helping these teams save a lot of time and effort so they can focus on the things that really matter to the business.

Shamil Malachiyev: Also, Kevin is extremely modest. He and his co-founder Taylor have raised over 15 million from Khosla and Madrona to build their vision, and their integration with Slack is pretty much going to revolutionize the industry for the new kind of companies and startups that are moving into AI integrations. So what do you think when you look at the industry? Because we have all these giants, like ServiceNow. How do you plan your strategy around those?

Kevin Coleman: Yeah, it's a really great question. And you mentioned we've raised some money; we get that question a lot. We are super fortunate to have been backed by some amazing venture capitalists: the folks over at Khosla, the folks over at Madrona, Founders' Co-op, and a suite of awesome angels as well. Shout out to all those people. I can't tell you how much we appreciate that support.

So, it's interesting when we look at the landscape. Enterprise service management is the category we operate in, and you mentioned ServiceNow; they are certainly the giant on the hill, so to speak. They've built a huge business helping companies with service management. It's a super large market that, in my opinion, is a little bit unheralded. Markets like CRM and some other categories get a lot of attention, maybe because more people are familiar with sales and everybody touches CRM. But enterprise service management is a huge category in its own right. Effectively every company, after you become 200 people in size, needs this type of software to help organize and automate the internal operations work the company needs to survive and to thrive. I really look at the software we're building as the grease in the enterprise gears. It's how the sausage gets made. It's how collaboration happens internally. It's how that work gets organized.

It's funny where this idea originally came from. I spent four years at AWS, and internally, Amazon has a system called SIM that they built that does a very similar thing. It's an amazing tool. It's very bare-bones, very basic. And I recognized how critical this was to the enterprise as a whole at Amazon. And I thought: what does this tool look like if a startup builds it that cares about design and user experience, cares about integrating this type of tool where people are already working, which is Slack, and, back then, 2024 going into 2025, cares about automating things with AI and leveraging all this new technology?

This space is quite competitive. There are a lot of incumbents. There are three areas, the way my co-founder and I talk about it, three legs of the Ravenna product stool, that we are going to be excellent at, and if you need these, you should probably come talk to us. Number one, you already mentioned it: deep Slack integration, and really it's a team chat integration. We've got a very strong thesis that the support portal for your employees, where support is provided and where help desks are, is Slack. Your employees don't want to go to some ticketing portal and fill out a form and wait for days to get support. They just want to type a message into a Slack channel and get their request resolved, whether that's via human or via AI. So, number one, we are building the best-in-class, and really best-in-industry, Slack integration, and we're super proud of it. I've actually built large swaths of our Slack integration, and it's pretty badass.

The second piece is practical AI and automation that leverages your existing data. A lot of our competitors have AI, and they'll do things like RAG on top of your knowledge base to answer repetitive questions, but it works really well only within their walled garden, i.e. if you use their knowledge base. We don't have a knowledge base in Ravenna. We work backwards from customers, and the overwhelming piece of feedback we got from customers was: look, we've got knowledge bases everywhere. We've got it in Notion, we've got it in Google Drive, we've got them in Confluence, we've got web pages. So we play really nicely with all of your existing data, and we bring that content into our system, we keep it up to date, and we sync it. And then we give you really great answers and insight on top of your existing data. So practical application of AI is where we're going to be really good, and we deliver excellent, high-quality, contextually relevant answers to questions.

And then the third piece, and this is a little subtle but really important for internal operations folks: out-of-the-box, beautiful analytics that are flexible and allow you to communicate to your team, your org, your leadership the value that your internal operations team is bringing to the organization. That was a lot, sorry. I don't know if you want to dive in on any of those.

Shamil Malachiyev: What I like the most about your team is that both you and Taylor are highly technical. You spent, I think, four years at Amazon; Taylor spent some time at Zapier working on AI. And when I look at the classical founding teams, it's usually somebody who's not technical performing the role of CEO. How do you juggle all of the functions between yourselves, both being highly technical?

Kevin Coleman: It's a really good question. The short answer is, we've actually made a change recently that delineates responsibilities a little more strongly. For the first year of the company, it was very much: let's do whatever needs to get done on a weekly basis to push the ball forward. The large part of that was really three things: recruit an excellent team, build the product, and work with our early design partners as closely as possible, and just rinse and repeat every week.

The team is up to 18 people at this point. We have gone beyond the design partner stage and have legitimate customers as well, and we have a product at this point that we can sell. So recently I've switched: I've thrown off the shackles, or moved out of the engineering organization, so to speak, and I'm one hundred percent focused on go-to-market. One hundred percent focused on sales, marketing, how we make the world know about Ravenna. That was just a conversation between us: look, we think we're ready to sell this product, and it's a founder problem to go figure out that go-to-market, especially in the early stages of a company. One of us had to own it, and I said, I want to go do this. This seems really fun. It seems like a puzzle to solve, and it's super important to the business.

And also, if I'm honest, Taylor is the best technical mind I've ever worked with. He's an incredible leader. The guy can build anything, and people love working for him. You talk to anybody at Zapier, they loved Taylor over there. There's nobody else in the world I would rather have run an engineering team than Taylor. So that's how we, as of last week, literally, split up responsibilities. He's doing product and engineering going forward, and I'm doing all of go-to-market, until such time in the future when we decide to change things up. Which I'm sure will happen, because things change rapidly in startups.

Shamil Malachiyev: And how do you find early-stage B2B sales? Did you have any assumptions going in, any challenges you didn't expect?

Kevin Coleman: You know, I wouldn't say there are challenges I didn't expect. The long and short of it is: it's hard, and it's a grind. Especially when you're in a category like ours, and you've chosen to build a product like ours, where there are existing players. We're not building ChatGPT before ChatGPT came out. There are competitors in this space, and you've got to sell against those competitors and answer the questions like the one you asked: how do you differentiate yourself, and how do you get potential buyers excited about buying your product as opposed to any number of legacy players that exist?

The first problem, though, is just making people aware of the company. How do you get yourself in the ballgame, so to speak? How do you make sure potential buyers are aware that Ravenna exists? And that is more of a marketing challenge than a sales challenge. I have a good amount of sales experience between the startups I've been at and my time at AWS, but marketing in a startup is definitely a new muscle. So you hire for the things where you don't have coverage: we hired a head of growth with a marketing and advertising background who's definitely helping out there.

One of the things we think about a lot is how we get our name out there, and one of those ways is content. Doing things like this podcast. We actually have our own podcast, which you might be getting invited to come on at some point. So we've got the Ravenna podcast, which we're going to be publishing over the next couple of weeks. We're doing a lot of stuff with our blog, a lot of stuff on LinkedIn. There's a line of thought that startups have to be content companies that happen to monetize via software nowadays. At least that's how I think about it. Because you have to figure out a way to stand out, a way to reach your potential buyers, especially in an environment like today, where there are so many new AI-native companies getting funded, and if you're a potential buyer, it's hard to figure out which of these companies to pay attention to. So, long story short: it's a grind, man. It's all about hustle, and about trying to figure out creative ways to reach your buyer, get meetings on the calendar, get demos, so you can showcase all the awesome stuff you're building.

Shamil Malachiyev: Does the content game come easy to you?

Kevin Coleman: Oh no, it certainly does not.

Shamil Malachiyev: We've all seen the videos on LinkedIn of you doing, I think, seven showcases of Ravenna features.

Kevin Coleman: Yeah, the launch week videos. So, if you go look me up on Instagram or Facebook or anything like that, I'm not there, because I just didn't really do social media prior to Ravenna. Friends around town tell me: man, you're all over LinkedIn now, I've never seen this from you. And I'm like, yeah. As a founder, you've got to become the cheerleader of your company, and kind of surrender your persona online, effectively, to further your company in whatever way you can. So it's definitely a growing muscle. It's something I'm getting more comfortable with, I would say, but it definitely doesn't come naturally to me. And where I see some content creators and CEOs of companies where it looks like it's easy, I'm sure behind the scenes there are people helping them: people helping them write content, come up with ideas, all that stuff. And we've got support in that capacity as well.

Shamil Malachiyev: That's a part of the entrepreneurship journey I love to hear about, because I believe that for some people, some things come more naturally. That's why we have natural CEOs, natural content creators like Gary Vaynerchuk, for example; it comes easy to him. But for other founders, we know that this is something that will propel the company forward, we know it doesn't come naturally to us, and we have to find a way to still do it. Because that's your job as a founder, right?

Kevin Coleman: It is. It's totally your job. We actually got really lucky. You mentioned Gary Vaynerchuk; there's a guy named Chase Jarvis, who is kind of Gary's vintage of early-internet successful content creators. And Chase is actually our landlord. He's a Seattle guy, the coolest guy ever. He started his career as a world-famous photographer, ski and outdoor photography, in the early 2000s. You can go look him up; he's awesome. And then he became CEO of a company called CreativeLive. He also had a really great podcast and a YouTube channel about being creative, about photography, all of this.

We lucked out. We ended up finding this office space, which is his, and we're the only tenant here, and he's become a friend of ours. A couple of months ago, at the beginning of the year, when we first started being in his office, we were telling him how we wanted to create this content and figure out this whole ballgame. And he was like: guys, let me help you out. I know how to do this. I've built huge communities. We bought some equipment with him; this mic, it's in his office, we share this mic with Chase. Have you heard of him? Check him out; his content is awesome, and he's got a very cool podcast.

He was basically like: look, you guys have just got to do it. Your first podcast, for example: you need to record the first podcast to get to the second one. And when we were scheduling the first one, we were hemming and hawing and not getting it on the calendar, and he finally just said: guys, get in the studio, which is in the room right over there. Get in the studio and record it. You're going to be bad, and that's okay. The point is, get the first one done so you get to the second one, and you learn and you improve and you do that over time. So we've had a little bit of a cheat code there, I think, in the sense of a guy in our corner who knows how to do this. But content's hard, man. It's hard, especially for somebody like me who likes to be a little more in the shadows. But you've got to do it for the brand, for the company. And it can be fun at times. It's fun having conversations like this with you.

Shamil Malachiyev: Yeah. But to get to this point, we have to go through the scary part, because there are all these challenges we have to solve psychologically within. For us, being out there with content is scary for some reason. For others, it's not. And once you start doing it, you actually realize there's so much fun in these connections and conversations.

Kevin Coleman: For sure, for sure. That is one of the benefits. It is fun. The internet facilitates these strange connections that end up being great. You reached out to me on LinkedIn: hey, we should do something. I'm like, yeah, we should do something. Now we're doing a birthday pod. It's great how things like that happen.

Shamil Malachiyev: What's your favorite part about Seattle?

Kevin Coleman: Oh man. So I'm a Seattle kid. I was born in New Jersey, but my family moved out here when I was six months old. I grew up here, moved away for a little bit of time, but now we're back. My wife and I, our families are both from here; our kids are going to grow up here. I love Seattle. My favorite part about Seattle is that I love doing things outdoors, and the outdoors here are so accessible. It's very easy to get to the mountains, very easy to get to the Sound, very easy to get to the lake and go swimming. The outdoors in Seattle are extremely accessible and world-class.

It's one of the contrasts I draw between Seattle and San Francisco. San Francisco is on the Bay, but it's hard to access the water. The water is cold, you don't want to swim in it, it's hard to get on a boat, it's expensive to have a boat down there. Whereas in Seattle, the lake is right here. Everybody's on the lake in the summer. There are plenty of beaches; you can just go swimming. Same thing with skiing: there are amazing mountains an hour or two outside of Seattle, and in the Bay Area you've got to drive to Tahoe for four hours if you're lucky, fighting traffic. Everything outdoors feels inaccessible down there, whereas in Seattle it's great. I feel like we're always outdoors, especially in the summer, when the weather up here is just amazing. So yeah, the outdoor aspect of Seattle is definitely my favorite.

Shamil Malachiyev: And during stressful moments building companies, or even before starting Ravenna, how do you clear your head? You talk a lot about being outdoors. Do you have any special practices?

Kevin Coleman: In the past, it was definitely fly fishing for me. Fly fishing is like meditation. If you've ever done it: the rhythm of casting a fly rod, and being out in nature in solitude. That's definitely my top way to unwind. I don't have much time to do that anymore, between my work and my kids. So spending time with my family is the way to unwind now, despite the fact that my kids are two, four and six, and an absolute handful, and crazy. They are a very great way to take my mind off the company and everything going on here, and to ground me back in what is the most important thing in my life, which is my family, and their health and happiness. So the way I unwind is basically by spending time with my family and being able to detach myself from the company a little bit.

Shamil Malachiyev: How has your life changed since you started having kids?

Kevin Coleman: Drastically, I would say. It's funny, you go through this progression. Do you have kids, by the way?

Shamil Malachiyev: We're about to start. Not yet; we're just planning now.

Kevin Coleman: Amazing, man, amazing. So, your first kid comes, and you think, oh my gosh, there's so much work having one kid, it's crazy. And then the second kid comes and you're like, one kid wasn't that crazy; two kids is nuts. And then the third kid comes and you're like, man, one kid was nothing. The way I describe it is: you surrender your personal time, more and more of it, the more kids come, to the point where by the time you have three kids, your personal time is basically gone. Your personal time is your family time now, your kids' time. You're not living as much for yourself now as you are for your kids and your family. It's this weird psychological thing that happens where your priorities just rapidly shift. Everything before that is me, me, me. You might get married, and it's you and your wife. But after you have kids, it's all about your children.

Shamil Malachiyev: And how did you go through that transformation internally? Because prior to having kids, you probably had an internal, maybe a little selfish, side that wants your own time, your own space. There's work, but then there's time for Kevin. And now that you have kids, you have to surrender that part of yourself and develop something new.

Kevin Coleman: For sure. You have to. I think every new parent goes through, and this might sound like a bad way to put it, the grief of losing your free time. But then your kids come, and you realize: wait, my selfish free time wasn't even nearly as cool as hanging out with my kids, especially as they get older. Once you're on the kid train, things just get better every day as they get older. The first six months, for a dad, you've got a little baby, you can't really do anything; they're attached to their mother. But after that, everything gets better every day. They go through the extremely cute phases where everything is very cute, and then they get older and start doing things like playing sports and dancing and all the fun things, and you get to go through that with them. And you realize: this is way better than whatever the heck I was doing in my early twenties or early thirties. That was still fun, but nothing compares to raising and spending time with your kids and watching them grow. It's a transition every parent goes through, but I don't know what's better in life, to be honest with you. I haven't found anything yet.

Shamil Malachiyev: Did you bring any lessons from the way you were brought up as a kid into your parenthood now?

Kevin Coleman: Yeah, definitely. My dad has a saying: there are three things he had to give his kids. I have four brothers, so there are five boys in my family. Crazy, crazy household to grow up in; a bunch of maniacs. Three things: please-and-thank-yous, so manners; a good education; and good teeth. That was my dad's three things, for whatever reason. So we all had braces for years.

But the please-and-thank-yous, I think, is more about how you raise good human beings, who are kind, who are compassionate, who treat people the right way, who are polite, who are just good people. And that's something my wife and I very much care about: raising whole humans who are kind people, thoughtful people, curious people. I think my parents did a great job of that with my brothers and me. You and other people can be the judge of that. But I definitely take learnings from them, and I think back fondly on my childhood, and I want to give my kids a similar childhood to what they gave me.

Shamil Malachiyev: Were you the oldest, the youngest?

Kevin Coleman: I'm the middle, straight in the middle. I have two older brothers and two younger brothers. And we're all in Seattle, which is great. Well, four and a half of us are in Seattle; my youngest brother splits his time between New Orleans and Seattle.

Shamil Malachiyev: Since you were a kid, did you have a lot of competition with them? Do you feel very competitive?

Kevin Coleman: Oh yeah, 100%. Absolutely. Very competitive. I don't think you can have five boys who are playing sports all the time and not be very competitive people. The house was always playing sports, always yelling and screaming: I won, you won, no you didn't win, all that fun stuff. We actually celebrated my older brother's 40th birthday last weekend; he's a year older than me, and he's my best friend in the world. And we were talking about how, growing up, we actually weren't very close friends, because we were quite competitive, and he loved needling me. He was just better than me at everything: better at sports, smarter in school, way better than me, and he loved letting me know it. It would drive me crazy as a kid. But then you grow up and you mature, and you realize: wow, we actually really like each other.

Shamil Malachiyev: So, two things I've noticed: one, you develop really good social skills, because you have a lot of people to talk to when you're young with your brothers. And the second is something that provides some sort of motivation as you get older.

Kevin Coleman: In terms of competitive motivation? Maybe. The social skills thing, probably. One of the things with my kids: my oldest daughter is six, and we say she's six going on 30, because she'll have full-on conversations with adults, and adults are like, what is this six-year-old kid having a full-on conversation? I think that's because she hangs around my brothers a lot; she's always with adults. So maybe being around that many people has helped with social skills.

On the competitive nature: I'm not sure, to be honest with you. I'm definitely competitive in a business sense. I want to win, straight up. And I don't think you want to go start a business unless you have that competitive side, because it is such a grind, and it's so hard, and you have to want to win, and you have to want to make an impact in order to be successful doing this. For the most part; I'm sure there are exceptions to that rule. I don't know if that competitiveness comes from growing up. Maybe it does. Maybe it helped.

Shamil Malachiyev: And have you found your why? Your real internal motivation that drives you?

Kevin Coleman: I think my why has probably changed over time. This is the second company I've started; the first one we started back in 2016, same co-founder. Back then, I feel like there were a number of whys. I like figuring out how systems work, how things work. I mentioned fly fishing earlier: when I first got into fly fishing, I wasn't so much interested in the catching-the-fish aspect. I just wanted to figure out how to do it. How the flies were put together, how to make your own flies, what kind of lines you need, what kind of rods you need, how the current worked, how you need to read current, where you need to be in order to catch these fish. It was a system I had to put together, a puzzle I had to figure out. And I find that I like doing that.

Company building is like that to a certain extent. I feel this insane need to figure out how these games work: how to build a company, how to hire people, how to acquire customers, how to build product, and how all those pieces come together to produce a brand that people love and a product that companies can buy. Figuring that out is a thing. Delighting customers is a thing. Being successful as an individual in your career is a thing. So there were all these probably extrinsic motivations earlier on.

Now, my why is one hundred percent my family and my kids, and being successful for them. Not only providing them the life I want to provide for them, but also showing them what hard work looks like, and that you can just do things if you want, if you're willing to take risk, and if you're willing to put yourself out there enough. They're really young now, but they'll grow up as we're doing this company, and they'll see the things that I have done. My wife works too; she has a thriving career at Nordstrom. I want them to understand the value of hard work and the things that can come from it. I don't think there's one thing I could point to as the root reason I'm doing this. But if I had to point to one, it's very much trying to be the best I can be for my family, and in particular for my kids.

Shamil Malachiyev: What kind of person do you want to be for your family?

Kevin Coleman: It's a hard question, man. I want to be as good a dad and husband as I can be. It's hard to be the best you can be at all times with everything going on at a company. But I want to be present for my kids. I want to make time for my kids. I coach my son and my daughter in their sports, and I make sure I'm there to do those things. I definitely will not be the absentee entrepreneur dad. You hear about people who get divorced because they're so ingrained in their company that it destroys their personal lives. That will absolutely not happen with me.

I'm actually fortunate, because my co-founder Taylor has two young kids as well. The biggest difference between the first company and this company is that there were no kids then. Well, actually, he had his first kid right after we started the first company. But now we've got five kids between us at this company. For us, being an excellent dad is priority number one, straight up. It's hard, juggling the time the company requires while making sure you're a great husband and a great father. But it's critically important to us. And I think that's important to the company as a whole as well, because the people we hire need to know that's a priority too. Despite the fact that it's a startup, and we are going to work our asses off to make this company successful, you are still an individual at the end of the day, and you still have family that matters to you and people in your life you've got to take care of. That's something we care about as founders of the company: that you're able to do that at Ravenna as well. And it's something we talk openly about with people when they're considering joining the company.

Shamil Malachiyev: What are some other aspects of the culture you look for in the people you bring on board?

Kevin Coleman: So, at Amazon, Amazon's got their Leadership Principles. I'm not sure if you've ever seen them, but if you talk to anybody who's been at Amazon, it's like religion there. When you're interviewing, they tell you: go study the Leadership Principles, this is what you're going to be interviewed on. And you'd think, going through the interview process, that after you get in, you're not going to talk about them at all, that it's a dog-and-pony show to get into the company. But in reality, everybody lives and dies by these Leadership Principles at Amazon. They're talked about every day. It's a great framework for making decisions.

We don't have Leadership Principles here, we don't call them LPs, but we have values, and it's the same concept. You want your business to have values that your team understands, that you communicate to people joining the company, and that act as guardrails for how the company operates and how you make decisions.

A couple of the values we have at Ravenna: we phrase it a little differently, but effectively a bias for action, a bias for decision-making in the face of uncertainty. We care about high-agency people who are able to act autonomously and make good decisions independently. We would much rather people move forward and course-correct down the line, as opposed to sitting there waiting for somebody like Taylor or myself or somebody else in the company to make a decision for them.

That relates to another of our values, which is speed. The only advantage you have as a startup is your ability to go at a breakneck pace. You're never going to have more money than your competitors. You're never going to have more technical talent, for the most part. You're never going to have as good a product moat; you're never going to have as good a distribution. But what you can do is outpace these guys all day long. And it's speed across decision-making, speed across how you communicate with customers, speed across how you build product, how quickly you're responding to people. The clock speed of the organization has to be so high. So we look for people who have an internal sense of urgency, and that's a hard one to interview for. But you want people in a startup who viscerally get on board with the thought process that if we don't move as fast as possible, we're going to die: the company will cease to exist, and we're going to have to go find other jobs. You look for people who have that engine and that motor, that internal motivation, who just want to go fast and build stuff really fast. The people who hate corporate bureaucracy and culture, who are in big companies losing their minds because they can't get stuff done: if you're that type of person, come to a startup, man. You're going to be able to go as fast as possible, and you're going to be happy.

We also care about people who are effective communicators, especially in a remote setting, and who enjoy collaborating with the team. We've got a third of the team in Seattle, two thirds dispersed around the US, and some folks overseas. You have to be an active participant in the company. Practical things, like being actively visible in Slack. You have to communicate effectively in a way that is almost unnatural: continuously check in through the day, see where you can help, make sure people are aware of where you're at, what you're working on, the help that you need. Active communication and participation, and a willingness to do that, not just sitting in a hole doing your code, but being part of the team and part of pushing the team forward, is something we highly value as well.

Shamil Malachiyev: I wanted to ask what kind of role aggression played in your journey, in becoming an effective founder who protects the culture and can use aggression as an energy for good.

Kevin Coleman: I don't know if aggression is the right word. I get what you're getting at.

Shamil Malachiyev: Assertiveness.

Kevin Coleman: Assertiveness, for sure. But maybe obsession might be a better word. I care desperately about this. I'm obsessed with this logo here. I'm obsessed with Ravenna. And it's not just building a successful company. I'm obsessed with getting the best people in the company to help us win. I'm obsessed with building the best product, one that is beautiful and a delight to use, that customers love. I'm obsessed with figuring out how to acquire customers in a cost-effective way, figuring out that puzzle. And I'm obsessed with building a culture that we all collectively love.

Taylor and I say this thing: we want Ravenna to be the coolest place to work if you're in Seattle and you're a technology person. We want everybody to say, man, I want to go get a job there. We're definitely not there yet, but we're working on it. You've got to be obsessed with this stuff, obsessed with putting the puzzle together, and that obsession makes you hold a high bar. It makes sure you've got really high standards across all these areas. I think at times people can get frustrated with people like me, or other founders, who've got that really high bar and want things to be really high quality. But everything that touches the company and the brand matters at the end of the day. Every LinkedIn post I put out matters. Every video clip we put out matters. Every blog post matters. Sometimes you can get mired in "good enough", and good enough, for an early-stage startup, is often not going to be good enough to win at the end of the day. So yeah, I think obsession might be the better word than aggression.

Shamil Malachiyev: It's one of the best and strongest qualities I identify in founders who actually make a difference and build big companies. I've definitely had a few people in my career who were afraid of being seen as not nice, and they would see something they didn't like and internalize that frustration, unable to actually speak out and correct things when they obviously needed to be corrected.

Can we go back to your journey before Amazon, when you and Taylor started Mesh Studio? Can you tell us how you and Taylor decided: that's what we're going to do?

Kevin Coleman: Yeah, man, we're going back. So this was nine, ten years ago now. Taylor and I have a long history of working together. We both quit our jobs in finance to get into technology, totally independently. We got connected by a mutual friend of our mothers and realized we were doing the same thing. This was before the coding academies and the MOOCs of the world came out. So we said: all right, let's just help each other. That kicked off our collaboration.

We both went down to San Francisco and got jobs at startups around the same time. I went to a company called Layer; he went to a company called Chariot. His company was more successful than ours: they got bought by Ford. Layer had a good run but ended up shutting down. While we were down there, we got immersed in startup culture. We saw the people around us raising a bunch of money and building companies, and, to quote the meme, "you can just do things". It was that attitude: look, we're the ones actually building the products that our companies are selling and making money on. We know how to do this, to a certain extent. Why don't we go and try? So we applied to Y Combinator and got into the YC fellowship, and we did that for the summer. The original product was called Mesh Data, and we were building what is now known as a reverse-ETL platform. We didn't know what we were doing, though. We didn't know how to sell. We didn't know how to talk to customers. It was kind of dead on arrival, to be honest with you, but a very good learning experience. And we have an amazing network of people through YC now.

Shamil Malachiyev: Can you tell me about some of those experiences? You went through them quite quickly, but I can imagine there were a lot of frustrating moments and challenges you had to overcome.

Kevin Coleman: For sure. I distinctly remember going down to the YC offices for the kickoff day and being mortified, or petrified, I guess, would be the word, because you feel such strong imposter syndrome. You get into YC thinking: this idea we're building is really cool, and it's good. And then you get down there and meet all these other high-agency founders with all these crazy ideas, and you think: wow, is my product any good? Is what we're doing actually good? Or did they just make a mistake on me, slip me in there, and we're not really supposed to be here?

Shamil Malachiyev: And then you realize everyone else feels the same.

Kevin Coleman: Yes, exactly. Although there were some pretty awesome people in our class. One of the guys, I think his name is Zach, we met him out in the parking lot. I think he was a biologist, and he was making a hangover cure. He was like: I figured out this way that a chemical can break down the proteins, or the enzymes, or whatever it is your liver secretes when you drink alcohol, and I can help you not have hangovers. And I was like: that's incredible. Hard science. Of course you should be here. And his company is still thriving today, which is awesome.

The program was like a pressure cooker, because you feel you need to deliver and acquire customers as rapidly as possible. And it became pretty evident to us pretty fast that we didn't have an ICP. We didn't know who we were selling to, and that's one of the critical things you've got to figure out in the early days of a startup. We didn't even know the problem we were trying to solve very well. We had this developer problem: all this customer data needs to get into all these SaaS tools, so let's build an integration platform. We would go around to customers, and our pitch would be: hey, you have customer data problems, let us help you solve them. And everybody would say: of course we have customer data problems. But all the problems were different. We didn't know how to drill in and identify a specific thread, a specific pain, that was generalizable across a lot of customers that we could go and solve. We were just immature in how we talked to customers, how we dug for pain, the product management aspect of it. Shortly after YC, we realized it wasn't going to work. We also didn't know how to raise money, didn't know how to do the company thing. And if I'm honest, I think we were a little bit scared at the time as well. So we rapidly flipped the company into a consultancy, which ended up working out well.

Shamil Malachiyev: I looked at the Wayback Machine and saw the landing page. The two cases you showcased were Staples and August. Can you talk about those deals?

Kevin Coleman: August, yeah, August Locks. The Staples deal was wild, and that deal basically made our company, to a certain extent. The product I was building at the startup in San Francisco was an SDK you would put into mobile apps to add chat to your application. If you wanted to add chat, you could add it in a day, and Layer had all the backend infrastructure, so we made it very easy for you.

Staples had this innovation lab in Seattle that was experimenting with AI back in the day: intent and entity recognition type AI, not all the LLM stuff we have now. They were building chat into their application, and they wanted this thing they called the Easy System. Do you remember the easy button? The button you'd press, and it would say, "That was easy." It was this big marketing campaign Staples had back in the day. If you Google the easy button, it's a physical red button that says "easy" on it. So they were trying to build this AI system called the Easy System, and the idea was that you could chat with the AI to order products. They were struggling to get the SDK integrated. And the CEO of my previous company called me and said: hey, do you guys need any work? We had just shut down our company, so we did. He said: these guys need help integrating this SDK, can you do it? And I said: yes, of course. So we got our first contract there, and we did some good work for them, working with both Taylor and me.

Then they came to us and said: look, we've got visions of doing this not only with chat. We actually want to build a hardware button, the easy button, but like the Amazon Alexa, so you can talk to it to order products through Staples. We've been working with this offshore team to get this done, and they haven't been able to figure it out. We'd like you guys to build an external team for us to execute on this, if you want. The reason they wanted to do that, the way they told us, is that they had hiring caps internally for salary bands, and they couldn't get exceptional talent into the company. And what engineer wanted to go work for Staples at that time, if we're talking about really good engineers? But they said: we think you guys can probably hire people better than we can, and we have a different budget we can allocate to contractors.

So Taylor and I said: all right, great, let's throw out a big number and see if it works. Sam Altman had this quote at the time, something like: ask for things, because you never know if you might get a yes. Ask for big things. So we threw out a number we thought was really big, and they said: great, go do it. We signed a contract; it was a seven-figure contract. We were like: wow, this is crazy. So we were off on our way, and we had to go hire a team.

We worked with two amazing hardware companies, one who designed the hardware and one who did the firmware and low-level software, down in San Francisco. We built out the entire software side of the stack. We built a streaming audio protocol so we could stream audio in real time to our backend. We worked with a bunch of Watson APIs, funnily enough, because they had agreements with IBM: Watson APIs for speech-to-text and text-to-speech and all the intent and entity recognition. And we built a big logic engine on the backend to route requests appropriately to Staples' APIs. So that at the end of the day, you could say: "Hey, Easy, I need to order blue pens", and it would respond in under a second and say: "Great, I've added blue pens to your cart."

And we did it. We got it done. It was fun. We went down to the World of Watson conference about five months later, and the easy button was the belle of the ball. They were on stage with Ginni Rometty, showing big images of the button. And that contract effectively enabled us to hire our team, gave us runway to be selective about the other customers we would work with, and kind of got the company off the ground.

Shamil Malachiyev: And what was the strategy for growing Mesh at that time?

Kevin Coleman: Not a ton of strategy, man. It was basically: let's work through our network and find customers wherever we can, making sure people were aware that we're a business now and we're in play. One of the biggest failings I have from that journey, and if anybody's listening to this and wants to run a consultancy: when you do a consultancy, you have to be very specific about what you're excellent at. You should be an iOS company, or a Node.js company, or a hardware company, whatever it is. You've got to be very specific, because when companies hire consultancies, they want to hire the best in the world at that thing. We were very generic. We would come in and say: hey, we're software engineers, we're a software consultancy, we can build anything you want. We thought that was the right thing to do, because we didn't want to miss deals. We could build iOS, Android, web, backend, whatever you want, we'd figure it out. But that's not what the buyer wants to hear. That was the biggest mistake we made out of the gate. We got Staples and we got August Locks, so we were effectively an IoT consultancy, but we didn't want to brand ourselves as such. We totally should have. I think it would have helped in a big way.

Shamil Malachiyev: I'm writing this down, because at the moment I'm running an agency consultancy as well.

Kevin Coleman: Specifics help, man. Even now, with our company, you've got to be precise about what we do. Our product helps internal service teams deliver exceptional service to their customers via a modern ticketing system and our automation capabilities. Even that, we should probably be more precise about how we talk about Ravenna. I feel like you can never be precise enough, especially in the early days of a business.

Shamil Malachiyev: And that specificity helps you with the go-to-market structure, because it's easier to identify your ICP.

Kevin Coleman: It helps with everything, man. It helps with the assets you create. It helps with what you talk about. It helps sales cycles as well. Because when buyers have to work with you to figure out how they can leverage you, that's just more work you're putting on them. You want it to be very clear, when you come into a conversation, that your company is the best in the world at X, or one of the best in the world at X. That makes the buying decision that much easier.

Shamil Malachiyev: How would you advise consultancies or startup founders on positioning? How do you pick the right thing to be specific about?

Kevin Coleman: It's hard, man. Michael Grinich, who's the CEO of WorkOS, had something on LinkedIn the other day that I thought was really interesting. For the first two years of the company, WorkOS didn't make any money, and you sold to learn: you sold to understand what messaging worked, what positioning worked, and how customers reacted to the things you were saying. I thought that was really insightful, because you don't know how the market is going to receive what you're sharing with them and what you're telling them about your product. You have to learn over time, as you have conversations, and figure out what resonates.

So we experiment a lot. We're literally going through this right now: we have three verticals we target, which are IT, rev ops and people ops, and the messaging should be different for each of those, because their jobs and the things they do on a daily basis are slightly different, and the core workflows they need to automate are different. On every one of my sales calls, I spend probably the first 10 or 15 minutes just asking questions, because I'm constantly trying to learn: how did you find out about us? What did you think about our website? What were your expectations of our product before you came into this call? That's all gold. I've got an idea of what I want potential customers to know about Ravenna before they come into the call, and if they come in with wildly different expectations, that's a problem we've got to fix. I very much believe part of the early job of a founder is figuring out how to message this messy vision in your head to your customers in the most succinct way, so that they understand what you're trying to do in the way you want them to understand it.

Shamil Malachiyev: What I notice is that a lot of young, first-time founders, without proper experience of working for larger, structured companies where everything works, try to figure it all out by themselves. You had a bit of experience before starting Mesh, and then four years in a very well-oiled structure before starting Ravenna. What changed in you between those periods of your life?

Kevin Coleman: First of all, if you're trying to go it alone, I would just recommend not doing that. As I get older: when I was younger, I thought I knew a lot more than I did, and now that I'm older, I feel like I don't know anything. I'm hyper-aware of the fact that I have significant personal and professional gaps, and you've got to find people who can help you fill those. So finding excellent people you can hire and bring into your company is very important. But also, feedback is a gift. Whether it's negative or positive, you have to find people who will check you, give you feedback on the things you're doing well and the things you're doing wrong, and help shape you. I'm super fortunate that I have that with my co-founder Taylor. We've got that with our investors, with very open and clear lines of communication around feedback. I have it with our employees as well: an open door from a feedback perspective. I want them to tell me how I'm doing as a leader.

Over the last eight or so years of this journey: company building, to me, is very much a puzzle. You've got to figure out how the game works and how to put all the puzzle pieces together to build a good product, a good team, a successful company, a brand that's aspirational, that people really love. I'm constantly trying to learn, constantly trying to figure out how you do this. During Mesh Studio, we tried a bunch of things; a lot didn't work, some did, and you pick up some things and put them in your bag of tricks to pull forward. In my four years at Amazon, I learned a ton from amazing people who are super sharp and have done amazing things in their careers, and you pick up things there. And over the last year, since starting this company, we've learned a ton as well. It's almost like scar tissue. You accrue this stuff over time, and you build up this muscle of knowing how to react, and intuition around how to make decisions in a more effective and faster way. And I don't think you can read about that in a book. You can't get it via an MBA. You get it by being a founder, going through the grind, putting in the time, putting in the work. It just accrues over time.

Shamil Malachiyev: What are some of the biggest lessons you've learned that you wish you'd known before starting Mesh?

Kevin Coleman: Oh man, tons. One of the biggest ones we talked about already: being very clear about your differentiation as a company and how you exist in your customers' minds. A couple of really big learnings this time around: being very clear on who your customer is, and what problems they have, not even what you want to solve, but what problems they actually have that are acute enough that they will pull out their checkbook. That's priority numero uno for a person who's building a product.

Taylor and I have spent a lot of time, and effectively money, building software that nobody used and products that weren't successful. Technical people, engineers, bias towards building, because they can. They think: I just want to build something and get it out, and then I'll get people to look at it and give me feedback. But that's the wrong approach. The right approach? Go talk to a lot of customers before you write a single line of code. It's hard to find a lot of people on LinkedIn and get them to give you 30 minutes of their time. It's scary to reach out to those people. But you have to do it. Because you're either going to prove your thesis is right and learn a lot that will shape your roadmap in a meaningfully better way, or you're going to disprove your thesis and throw away the idea, which is equally important, because you won't spend months building and wasting all that time.

Before we wrote a single line of code for Ravenna, we went out and interviewed 30-plus people, because we needed to understand who our ICP is and what problems they have, so we could solve the right problems for them. You have to do that. No ifs, ands or buts about it, for company building. I've heard of founders who go out and talk to hundreds of customers before starting. That's amazing; if you can do that, you totally should. But at a minimum, you've got to talk to a lot of customers before you start building anything, because you have to be clear on who your customer is, what that ICP, that ideal customer profile, is, and what specific problems you're solving for them that are acute enough that they will give you money.

Shamil Malachiyev: You've now known Taylor and worked with him for around ten years. The kind of relationship you have, and the way you talk about him, is pretty much the union every founder wishes to have. What is the secret to making it work?

Kevin Coleman: Good question, man. I feel like, if you're fortunate enough to work with somebody as long as we have, you develop scar tissue. You've had all the fights you're going to have as co-founders, and you get to this point where there's just a ton of trust back and forth, and egos are out the window, and you are both completely aligned on the ultimate objective, which is building a successful company, and doing it while being good, kind people who care about the people in the organization and care about the customers.

I think lack of effective communication is the root of a lot of problems, that and letting ego get too far into the equation. There's a really good article on the internal YC forum; the person who wrote it has a company that helps founder relationships. He talks about how the root of a lot of founder conflict is the belief, from one side of the equation, that the other person is not pulling their weight, is not as invested, is not doing what needs to be done, from that person's perspective, to make the company successful. I've never felt that with Taylor. But being able to provide rapid feedback matters. You talked earlier about people who don't provide feedback fast and just internalize problems: that is failure mode, one hundred percent. You have to be comfortable giving your co-founder, your employees, whoever you're working with, feedback, and having a productive conversation: here's what I'm seeing, and I'd like to talk about it, to make sure my feedback is valid and we progress in a positive way, as opposed to letting it fester and letting frustration grow. One of the things I'm very thankful for with Taylor is that we are constantly giving each other feedback, positive and constructive, and we are constantly course-correcting each other to make sure we're performing as best we can.

So, in closing: if you find a co-founder with whom you can have that effective feedback conversation, get ego out of the room, and recognize that when somebody gives you feedback, it's in your best interest as a person, as a professional, and in the best interest of the company, and you're open to receiving that feedback and the other person is as well, you're going to have a good, constructive relationship. If you let ego come into the room, and you don't want to receive feedback, and you think you're the bee's knees who knows how to do everything and the other person doesn't know what they're talking about: from my perspective, that's failure mode. I feel very fortunate that Taylor and I have that relationship, and it's been productive and healthy for us for going on 12 years at this point.

Shamil Malachiyev: What are you most excited about for the next ten years?

Kevin Coleman: I'm just excited about building this company, to be honest with you. When you raise money, you always get questions about your exit strategy, which I think is a bad question, because at this stage of the company, unless you're some master fundraiser, master orchestrator, nobody knows they're going to sell their company in two years. You could come to me with any job in the world and say: hey Kevin, you could have this job instead of your job. And I would say no, because I don't want to be doing anything else. I love my job. I love what we're doing. I love our team, our customers, our space. There's nothing else I'd rather be doing professionally right now.

So when you ask me about exit strategy, or anything like that? There is no exit strategy. The only strategy is, we are going to make this company as successful as possible. We are going to work as hard as we can to build a large, consequential technology company. Try to make it the coolest place to work in the Northwest if you're a technology person. Delight customers along the way, help people grow in their careers, and build an awesome team. Hopefully we have this company for the next ten years and we can grow it into something that is consequential and enduring. That's the only thing I want to do, and building this business is what gets me really excited about the next ten years.

Shamil Malachiyev: Well, thanks so much for giving your birthday time today. You have a fantastic story, and you are an amazing human being. Thanks so much for coming on the show and sharing all of that today.

Kevin Coleman: Thank you, sir. Thank you for having me. I know it's getting to nighttime where you're at, so I hope you've had an awesome birthday, and I hope you have an awesome birthday eve. And yeah, man, thanks so much. This has been fun.